Abstract
1-Chloromethyl-1,2,3,4,5,6-hexamethylbenzenonium tetrachloroaluminate is investigated in an X-ray diffraction study. The crystals are monoclinic: a=8.910(2), b=12.290(3), c=17.654(4) Å, β=111.57(2)°, space group P21/c. The AlCl −4 anion has an almost perfect tetrahedral configuration; the average length of the Al−Cl bond is 2.130(3) Å. For cations, the symmetry is close to Cs. The C(2)−C(6) atoms lie in a plane (within ±0.012(5) Å), and the C(1) atom deviates from the plane by 0.113(5) Å to the side that is opposite to the CH2Cl group. Effects of the environment, as well as the effect of the nature of the R group, on the structure of 1-R-1,2,3,4,5,6-hexamethylbenzenonium are considered.
Similar content being viewed by others
References
G. I. Borodkin, Sh. M. Nagy, Yu. V. Gatilov, and M. M. Shakirov,Abstracts of Papers from the All-Union Conference on Diffraction Methods in Chemistry, Vol. 1, Suzdal (1988), p. 88.
V. A. Koptyug,Arenonium Ions. Structure and Reactivity [in Russian], Nauka, Novosibirks (1983).
G. I. Borodkin and V. G. Shubin,Usp. Khim.,64, No. 7, 672–703 (1995).
C. Baenziger and A. D. Nelson,J. Am. Chem. Soc. 90, No. 24, 6602–6607 (1968).
G. A. Olah and P. v. R. Schleyer (eds.),Carbonium Ions, Vol. 5, Wiley, New York (1976), p. 2427.
G. I. Borodkin, Sh. M. Nagy, I. Yu. Bagryanskaya, and Yu. V. Gatilov,Zh. Strukt. Khim.,25, No. 3, 114–119 (1984).
F. Effenberger, F. Reisinger, K. H. Schonwalder, et al.,J. Am. Chem. Soc.,109, No. 3, 882–892 (1987).
G. I. Borodkin, Sh. M. Nagy, Yu. V. Gatilov, et al.,Zh. Org. Khim.,28, No. 9, 1806–1826 (1992).
K. Schofield,Aromatic Nitration, Cambridge University Press, Cambridge (1980).
R. M. Roberts and A. Khalaf,Friedel-Crafts Alkylation Chemistry, Marcel Dekker, New York (1984).
V. A. Koptyug,Isomerization of Aromatic Compounds [in Russian], SO AN SSSR, Novosibirsk (1963).
V. G. Shubin, A. A. Tabatskaya, B. G. Derendyaev, et al.,Zh. Org. Khim.,6, No. 10, 2072–2080 (1970).
J. J. P. Stewart,J. Comput. Chem.,10, No. 2, 209–220 (1989).
A. A. Bliznyuk and A. A. Voityuk,Zh. Strukt. Khim.,27, No. 4, 190–191 (1986).
Yu. V. Zefirov,Kristallografiya,39, No 6, 1025–1031 (1994).
D. Heidrich and M. Grimmer,Int. J. Quantum Chem.,9, No. 5, 923–940 (1975).
J. T. Gleghorn and F. W. McConkey,J. Chem. Soc., Perkin Trans. 2, No. 9, 1078–1082 (1976).
T. Sordo, J. Bertran and E. Canadell, —ibid.,, No. 11, 1486–1489 (1979).
L. V. Vilkov, V. S. Mastryukov, and N. I. Sadova,Determination of the Geometrical Structure of Free Molecules [in Russian], Khimiya, Leningrad (1978).
Additional information
For the preliminary communication, see [1].
Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences. Translated fromZhurnal Strukturnoi Khimii, Vol. 37, No. 3, pp. 534–538, May–June, 1996.
Rights and permissions
About this article
Cite this article
Borodkin, G.I., Gatilov, Y.V., Nagy, S.M. et al. Comparative studies of the molecular structure of 1-R-1,2,3,4,5,6-hexamethylbenzenonium ions: Molecular and crystal structure of 1-chloromethyl-1,2,3,4,5,6-hexamethylbenzenonium tetrachloroaluminate. J Struct Chem 37, 464–469 (1996). https://doi.org/10.1007/BF02578602
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02578602